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Investigation of Iodonium Trifluoroborate Zwitterions as Bifunctional Arene Reagents. 2017
Raphaël Robidas, and
Vincent Guérin, and
Laurent Provençal, and
Marco Echeverria, and
Claude Y Legault
University of Sherbrooke , Department of Chemistry, Centre in Green Chemistry and Catalysis, 2500 boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
The synthesis of a new family of iodonium zwitterions, in which the formal anion is a trifluoroborate moiety, is reported. These reagents present very good stability and have high resistance toward benzyne formation. Their structures were confirmed by X-ray crystallographic analysis and were further investigated using DFT calculations. QTAIM analysis supports an ionic, noncovalent, I+···BF3- interaction, in accordance with a true zwitterionic nature. Preliminary results of synthetic applications, the arylation of phenolates and trifluoroborate group functionalization, are reported.
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